DIACETONE GLUCOSE ARCHITECTURE AS A CHIRALITY TEMPLATE .1. CRUCIAL EFFECTS OF THE INTRAMOLECULAR OXYGENS UPON THE LIALH4 REDUCTION OF THE PROPARGYL ALCOHOL OF 3-C-ETHYNYL-1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE DERIVATIVES

被引:8
作者
KAKINUMA, K
MATSUZAWA, T
EGUCHI, T
机构
[1] Department of Chemistry, Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo
关键词
LIALH4 REDUCTION OF PROPARGYL ALCOHOL; REGIOCHEMISTRY; REACTIVITY; SEMIEMPIRICAL MO CALCULATION; DIACETONE GLUCOSE;
D O I
10.1016/S0040-4020(01)96152-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The facile as well as regio- and stereoselective reactivity of 3-C-ethynl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose derivatives for LiAlH4 reduction into the corresponding ethenyl derivatives were investigated. The effect of oxygen atoms on the reduction is discussed by means of semi-empirical MO calculation.
引用
收藏
页码:6975 / 6982
页数:8
相关论文
共 22 条
[11]   MECHANISM OF HYDRIDE REDUCTION OF 1-ALKYN-3-OLS [J].
GRANT, B ;
DJERASSI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (07) :968-970
[12]   BICYCLO[2.2.1]HEPTANES IN ORGANIC-SYNTHESIS - TOTAL SYNTHESIS OF THE 16-MEMBERED RING MACROLIDE TYLONOLIDE HEMIACETAL - SYNTHESIS AND COUPLING OF THE C(3)-C(9) AND C(11)-C(17) FRAGMENTS [J].
GRIECO, PA ;
INANAGA, J ;
LIN, NH ;
YANAMI, T .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (21) :5781-5784
[13]   STEREOSELECTIVE SYNTHESIS VIA CLAISEN REARRANGEMENTS OF THE MARINE STEROLS OCCELASTEROL, PATINOSTEROL, AND 22,23-DIHYDROOCCELASTEROL [J].
HIRANO, Y ;
DJERASSI, C .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (12) :2420-2426
[14]   CHEMISTRY OF ORGANO-SILICON COMPOUNDS .173. REACTIONS OF ALPHA-HETEROATOM-SUBSTITUTED ETHERS AND SULFIDES WITH SILYL ENOL ETHERS - CHEMOSELECTIVITY IN THE CLEAVAGE OF HETEROATOM-CARBON BONDS BY IODOTRIMETHYLSILANE AND TRIMETHYLSILYL TRIFLUOROMETHANESULFONATE [J].
HOSOMI, A ;
SAKATA, Y ;
SAKURAI, H .
CHEMISTRY LETTERS, 1983, (03) :405-408
[16]   FACILE SYNTHESIS OF CHIRAL GLYCINE USING D-GLUCOSE AS A CHIRAL TEMPLATE [J].
KAKINUMA, K ;
IMAMURA, N ;
SABA, Y .
TETRAHEDRON LETTERS, 1982, 23 (16) :1697-1700
[17]   [2,3]-WITTIG REARRANGEMENT ON CARBOHYDRATE TEMPLATE - NOVEL-APPROACH TO CHIRAL SYNTHESIS OF 3-ALKYLMALIC ACIDS [J].
KAKINUMA, K ;
LI, HY .
TETRAHEDRON LETTERS, 1989, 30 (31) :4157-4160
[18]   SYNTHESIS OF CHIRAL ACETIC-ACID BY CHIRALITY TRANSFER FROM D-GLUCOSE [J].
KOBAYASHI, K ;
KAKINUMA, K ;
FLOSS, HG .
JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (07) :1290-1291
[19]  
MILLER CH, 1973, TETRAHEDRON LETT, P285
[20]  
RAO AVR, 1986, TETRAHEDRON, V42, P4523